项目名称: 过渡金属催化分子内脱羧和C-H键活化构建氮杂环化合物研究
项目编号: No.21302110
项目类型: 青年科学基金项目
立项/批准年度: 2014
项目学科: 数理科学和化学
项目作者: 杨道山
作者单位: 曲阜师范大学
项目金额: 25万元
中文摘要: 脱羧反应主要副产物为二氧化碳且具有较高的区域选择性;C-H键活化反应是一条更加直接并符合原子经济性的途径。脱羧和C-H键活化反应结合了脱羧偶联与C-H键活化的特点,符合绿色化学和原子经济性的要求,这种合成策略引起了研究者广泛的关注。本项目拟合成特定结构的反应底物,采用过渡金属催化分子内脱羧和C-H键活化反应策略构建六类氮杂环化合物:5H-吡咯并[2,1-a]异吲哚-5-酮、吡咯并[1,2-a]喹啉、5H-咪唑并[2,1-a]异吲哚-5-酮、H-咪唑并[1,2-a]喹啉、[1,2,3]三唑并[1,5-a]喹啉,8H-[1,2,3]三唑并[5,1-a]异吲哚;深入研究各类杂环化合物的环化机理,并将该催化策略应用到天然产物Luotonin A的合成研究中。本项目将构建具有较大容量多样性取代氮杂环化合物分子库,为氮杂环类药物先导化合物的发现提供重要的化合物来源和筛选平台。
中文关键词: 过渡金属;无金属;脱羧偶联;杂环化合物;含硫化合物
英文摘要: Carboxyl group in carboxylic acid ensures the regioselectivity of decarbonylation process with carbon dioxide as the major by-product. On the other hand, direct and straightforward formation of various function groups from unactivated C-H bonds meets the requirement of atom-economy and has emerged as a powerful tool for organic synthesis. Transition metal catalyzed decarboxylation and C-H activation combine these two green approaches and has drawn much attention in organic chemistry. In this project, we will design and synthesize substrates with special structure and construct six kinds of N-Heterocyclic Compounds via intramolecular tandem decarboxylation/C-H bond activation: 5H-pyrrolo[2,1-a]isoindol-5-one, pyrrolo[1,2-a]quinoline, 5H-imidazo[2,1-a]isoindol-5-one, H-imidazo[1,2-a]quinoline, [1,2,3]triazolo[1,5-a]quinoline, 8H-[1,2,3]triazolo[5,1-a]isoindol. Furthermore, mechanisms of the formation of every cyclics will be studied in details. Meanwhile, the new synthetic strategy will be applied in the construction of nature product Luotonin A. This project will establish a large library of various substituted N-Heterocyclic Compounds and provide an important screening platform for the discovery of the N-Heterocyclic drug lead compounds.
英文关键词: Transition-metal;Metal-free;Decarboxylative cross-coupling;heterocyclic compound;sulfur-containing compound